Third Time's the Charm
by SilverPedals1402
Summary: Confessing to the one you love can be either a hit or a miss. For Tony, it's been nothing but miserable misses and failures. But maybe the third try will be a hit instead of a miss.
1. Chapter 1

**Happy Valentine's Day! :D I almost made it on the day of, but an hour or two isn't that bad. I had some free time, and thought, hey perfect time to write a cute one-shot, which turns out will be made into a two shot, because I felt like it. :) **

**Disclaimer: IMAA doesn't belong to me. Marvel and Nicktoons or whatnot own IMAA.**

"How do you even manage to screw up that badly?" Rhodey asked, trying and failing to contain his laughter.

The two sat in Rhodey's house in the room that used to be Tony's room, but had been turned into a guest bedroom since his dad had returned. Tony sat on the bed, a fluffy pillow in his lap. Rhodey stood in front of the bed, holding his stomach as he laughed.

Tony, still red in embarrassment from the fiasco from earlier, groaned in his misery. "Will you stop bringing it up?"

Rhodey had been laughing at Tony's mistake ever since he first heard of it, which was hours ago. Tony was quick to regret telling his closest friend, who seemed to get quite the kick out of what most likely just became one of Tony's most embarrassing moments. What sucked the worst, was that it was all because he thought he was being sweet and kind, but turns out, he failed to even do that.

It all started during his free period, the one he gladly shared with his favorite redheaded girl. The one girl who somehow managed to steal his heart in the most agonizing way possible. At first it was gradual and pleasant, but then something changed. He didn't know what, but what ever it was, it hit him hard. He was suddenly seeing his friend in a whole new light, a light he had never imagined he'd be seeing her in. In the beginning, he was confused and unsure, but he still enjoyed the feeling. But after so much, he suddenly found himself falling for her and he was sure falling hard, like a dropping a cinderblock off of a ten story building.

And he'd only had this feeling now for a few weeks, but it was enough to drive him mad. So when a special date came, he felt that it was the perfect time to give into his feelings and give it a shot. He'd man up and tell her. He planned on telling her everything. Even if it was so cheesy it was hard to listen to. He'd tell her how hard he had fallen for her and how beautiful he thought she was. He'd tell her that he'd want her by his side for as long as humanly possible and as long as she could bear having him at her side. He'd tell her that her smile was best when she showed her teeth and that her smile blinded him every time she smiled. He'd even tell her that he could never stop thinking about her. It was going to be epically romantic. The best day of his life thus far.

But, when the moment came, he choked up. It went something like this:

"Pepper, there's something I've been wanting to tell you," he had begun nervously as he played with the fabric of his shirt.

He hadn't realized that she had been chewing something, so her reply was delayed. "Hmm?"

Apparently, she had a lot to chew on, so her cheeks were puffed out from whatever she had shoved in her mouth. He hadn't noticed that she had even brought any food up to the roof with them. The sunlight made her face seem like it glowed as her brown eyes watched him patiently and expectantly. She looked almost excited.

It was then that he realized the severity of what his words meant. What he had to say could either make it or break it for him and he wasn't sure if he wanted to find out which one. If he made his feelings known, it could change everything. Even as much as ruining their friendship if she didn't feel the same. It was the point of no return if he spoke the words he wanted to say.

_But it's Valentine's Day,_ he had told himself in encouragement. _That has to mean something, right?_

He took a deep breath. "Pepper, I don't know how, but I have fallen for you. And I've fallen hard. Your beautiful smile and your brilliant wits are something I just can't resist. Every time we're together, my heart does flips and my face gets warm. We've known each other for a while now and I don't know how I hadn't realized this sooner, but I think I might be in love with you."

At least, that was what he wanted to say...But instead this came out:

"You have something right here," he chickened out while pointing to her cheek.

Her hand shot to her cheek in embarrassment, all curiosity and excitement gone from her eyes. She swallowed the food that was in her mouth. "What?"

Tony had mentally slapped himself over and over again, before excusing himself to use the bathroom. But that wasn't exactly the embarrassing moment Rhodey was laughing at. No, it was Tony's backup plan that had gone so fatally wrong. Okay, maybe not fatally, but it was sill embarrassing enough.

His backup plan was very much so last minute and thought up on the fly. Because even his first plan was really just made up that morning. So during his time "in the bathroom", he took his time to create a quick letter. He thought maybe a letter would be romantic enough to make up for his failed verbal attempt. Then all he'd have to do was wait until she read the letter and then if she accepted, she'd come straight to him, hopefully excited and happy. Or wait until she came and slapped him for throwing a wall in their friendship.

His first mistake was forgetting to put Pepper's name in the letter. Which, wasn't so bad, because it was obviously for her. His next mistake was his lousy attempt at writing a romantic, non-clichéd letter. It was probably filled with too much cheesy quotes and a little overbearing on how he felt for her. His third mistake was forgetting to write his own name. Instead he accidentally left the end of the note as: _Love_. And that was it. But his last mistake took the cake.

It was the end of the hour, and Tony had walked Pepper to her locker, like the gentleman he was, or at least the gentleman he was trying to be. He walked off and decided that he wanted to see first hand what Pepper's reaction was. His stomach as tumbling and rolling and twisting, his heart was beating quicker the wings of hummingbird, and he found himself nervously shifting his weight on his feet.

He saw her open her locker and a slip of paper had fallen out on the ground. Tony watched anxiously as she bent over to pick it up. Then he waited and waited as she looked at it. But suddenly, all his anxiety and excitement was replaced by confusion, when Pepper just tossed he paper back insider her locker with no interest. She then shut her locker and headed to her next class.

For a moment, it felt like his heart was just crushed under a sledgehammer and dropped off a cliff. Did that mean she didn't like him back? Did she hate the letter? He couldn't understand where he went wrong. He tried to make himself clear on what his feelings were and he even tried to compliment her best features, because even he knew that girls liked to hear that about themselves. But did he go too far? Did she not like what he had to say about her?

"YES!" A sudden shout brought him from his troubled thoughts. His attention was brought to the girl who had a locker just next to Pepper's. She had red hair, which wasn't nearly as gorgeous as Pepper's in Tony's opinion, that bounced in her joy as she jumped in her happiness.

Her friend rushed over to her side with equal excitement. "You got a love letter? Who's it from?"

"I don't know, it doesn't have a name," the girl said, reading through the letter.

"Oh, a secret admirer!" the friend cheered. "And he likes your red hair!"

That was when Tony noticed it. The letter in the girl's hand, wasn't just any love letter. It was his love letter. His love letter that he had personally wrote specifically for Pepper. For her eyes only.

It took all his will not to let out a scream out of pure frustration. It was hard enough trying not to pass out from his embarrassment and failure. His letter to Pepper was now out for all to see, or at least all that this girl let see. All his personal thoughts and feelings were left open like a book to read. He felt so exposed, so vulnerable. No one else but Pepper was supposed to read that. It was meant for her and her only. But he had made the mistake of putting it in the wrong locker.

It wasn't until several minutes, after the late bell had rang, that he realized something. His name wasn't on the paper. Pepper's name wasn't even on the letter. Nothing pointed to any of them in the end. That he knew, because he memorized every word, every letter that he had wrote down in that letter. Nothing signified that it was him who wrote the letter and nothing pointed that it was intended for Pepper. It was a relieving thought if nothing else, that the letter at least couldn't be traced back to him. At least now, the girl can believe that she really did have a secret admirer and he wouldn't be hurting any feelings if he had to explain that it wasn't meant for her.

But the fact that he still forgot what locker was Pepper's, even when he stopped by it all the time, made the whole event all that more embarrassing. If anyone found out, he knew he'd never live it down. Now the whole school finding out, that would be nothing short of a nightmare.

But somehow, he had brought it up to Rhodey. At first, he thought maybe his friend could help him in his dilemma and help him figure out a new way to express his feelings to Pepper. but now, he couldn't figure out why he thought it was a good idea.

"How did you get her locker wrong, though?" Rhodey asked, stifling his laughter as much as he could. "Her locker is the only one with a red lock!"

Tony ran both of his hands through his hair in his frustration. "I don't know! I was nervous!"

Rhodey sighed, feeling bad for his friend. "Why don't you try telling her how you feel. Just keep it simple."

"I already tried," Tony omitted the part where he didn't exactly try doing it simply, "but I choked up."

"What did you do?" Rhodey wondered, curious on what else his friend could've messed up.

Tony went red for the millionth time in the passed five minutes. "Nothing."

"Your face doesn't say nothing," Rhodey stated.

"What should I do? I can't tell her how I feel and I certainly can't write how I feel!" Tony's shoulder slumped in defeat, ready to accept the fact that his idea of a perfect Valentine's Day wouldn't happen. At least not this year.

"Buy her chocolates," a high-pitched voice spoke. Tony just about fell off the bed, she had startled him so much. "Then make an indoor picnic while watching a romantic movie."

"Pepper, what are you doing here?" Tony asked, hoping that Pepper didn't know that they were talking about her.

"Roberta let me in," Pepper answered with a shrug, taking a seat beside Tony on the bed.

"Hey, Pepper," Rhodey greeted. "Anything exciting happen yet for your Valentine's Day?"

"Actually, this one guy in History class..." Pepper began cheerfully.

Tony interrupted her. "I don't want to hear it!"

He stood up and started walking out the door, deciding to give up on his plan entirely. He'd have to wait another time to let his feelings be known. Maybe now wasn't the right time.

Pepper crossed her arms in a pout and turned back to Rhodey. "What his problem?"

"He's having girl problems," Rhodey explained.

"I am _NOT_ having girl problems!" Tony snapped before stomping out of the room.

**I don't know where I got the idea, but I'm liking it so far. How about you guys? Like I said above, this will be a two shot, so the next chapter will be the last. **

**Fun Fact: _For some reason, I work better in a cluttered area. Whenever my room is clean, I can never find anything and it throws me off, but when my room is a complete mess, I find basically everything I need right away..._**

**Hugs and Love, SilverPedals! *Imaginary chocolates from me to you!***


	2. Chapter 2

**Since this was written in honor of Valentine's Day, I figured it'd be best to finish it up quickly. :) So this is the final chapter to my two-shot! Hope you guys like it! **

**Disclaimer: IMAA doesn't belong to me. We all know that!**

He couldn't figure out why, but the next thing he knew, he had stormed his way into a chocolate shop. It was as if his legs had gone into auto drive or something, because one moment he was in Rhodey's house, and the next thing he knew, he was surrounded by chocolate. Which, wasn't so bad since chocolate was very tasty. Pepper's words must have somehow influenced his actions, because now he found himself buy a box of chocolates. A heart-shaped box too. How adorable.

"For your lady friend?" the older man at the counter asked when Tony had handed the box of chocolates to him. "Better hurry, the day is ending."

Tony sighed, knowing full well what time it was. "She's not my girlfriend," Tony responded, digging in his pockets to see if he had any cash. "At least not yet..."

The man at the counter, Max according to his name tag, gave him a warm smile, small wrinkles on his face stretched. "Oh, how lovely. New love!" he laughed as he bagged the bag of chocolates. "I remember when I first met my wife..."

Tony nodded and smiled waiting for the man to hand him the bag as he offered up his cash. But the man had his story to tell. In the five minutes he had been there, he suddenly knew the whole love story between Max and his wife, Emily.

Finally, Tony was handed a bag of chocolates. "Thank you," he said politely handing the man his money.

"Oh no, thank you," Max smiled, before handing Tony back a few dollars. "Oops, it seems like you gave me too much."

"But..." Tony pointed to the screen in front of both of them that held the price of the chocolates. He paid just the right amount.

Max shook his head. "No, my boy, I'm sure you over paid."

Tony blinked, but couldn't find it in himself to argue. He thanked the man once more before heading out to his next destination. Which brought him to a movie store. Apparently he hadn't given up on his plan because not only had he just bought Pepper a box of chocolates, but now he was out buying her a movie as well. Which, he had no idea what kind of romantic movie she wanted. A tragic love story? A cheesy one? One in between?

After much debate with himself, he decided the best way to go at it, was at random. He was standing in the romance section along with a few other guys, and he picked out the first one he saw and then the second and then the third. At least then, they had a choice.

It was after that, when Tony found himself back home, staring at the clock. It was almost 6:30 in the afternoon. he looked at what he had to make sure he had everything. Chocolates, check. Romantic movie, check. Place to have indoor picnic, check. Food for indoor picnic, he wasn't so sure. He went to the fridge to check to see what food they had. Which, normally wasn't much because it was just him and his dad, and often times they got take out, because neither of the two had any clue on how to cook anything edible.

But when he checked, he found the fridge was almost fully stocked. Which, Tony admitted was more strange than he had expected.

"I went shopping today," his dad said, stepping into the kitchen. "Thought you might need it."

"What?" Tony asked, giving his dad the look of a deer caught in the headlights.

"You know, for your date," Howard said with a smile.

"Dad!" Tony complained loudly. "I don't have a date!"

"Of course you don't," Howard agreed, confusing Tony. "You haven't even invited her yet."

This time, Tony really did hit himself. Of all the things to forget, he forgot the most important part. He forgot that to have all this happen, he needed her to be there. Otherwise, nothing would have worked out. He was so worried about having food and chocolates and a romantic movie that he hadn't even thought about whether or not Pepper wanted to come or not.

"Right," Tony said, "I need to call her, don't I?"

Howard nodded. "I'd get to it, before she eats. If she hasn't already..."

"You're not helping," Tony commented, before pulling his phone out. "Now go away!"

Howard just shook his head with a laugh before waving. "I'll be in the lab downstairs if you need anything. And don't worry, I'll stay down there for the remainder of the night."

Tony blushed bright red. "Dad! We're just watching a movie!"

But his dad was already gone.

Tony just sighed and dialed up Peppers number. Hopefully she wasn't too upset with him about earlier, because now that he thought about it, he hadn't exactly been kind to her all day. As the phone rang more and more, his nerves rose. His stomach twisted in a knot. What was he supposed to say? Should he ask her on a date? Should he just invite her over? What should he say?

"Hello?"

"Oh! Uh...hey, Pep," Tony started. Yep, this wasn't going to go by smoothly. He cleared his throat. "How are you?"

He could hear the confusion in Pepper's tone as she responded. "I'm...fine, I guess. How are you? Did you solve your girl problems?"

"I'm NOT having girl problems!" Tony instinctively snapped, before sighing. "Sorry, I didn't mean to snap." He took a deep breath. He really needed to calm down before he completely blew his chance with her. "So um...you want to come over?"

Right. Because that was totally going to win her over.

"Okay," Pepper sounded happy, excited even. "I'll be over in a flash!"

Tony blinked. He hadn't expected her to accept so quickly, or at all... "Really?"

"Uh, duh!" Pepper laughed. "That's what I said, right?"

Tony felt so happy, he swore he could cry. But he wasn't, because he was stronger than that. "Right, yes! You did say that. So, I'll see you...?"

"Soon, I'll head out in five minutes," Pepper finished.

Tony checked the clock. Was that enough time to set up their little picnic. Speaking of picnic, what were they going to have? Tony couldn't cook, that he knew for sure. And he was sure that Pepper wouldn't appreciate left over take out. So that left...cereal? He shook his head quickly. He'd earn himself a quick slap to the face if he did that.

"Tony?" the girl that troubled his heart so much interrupted his thoughts.

"Sorry, what?" she didn't say anything important, did she? He had to wonder.

"Nothing," she replied, "I'll see you soon."

As soon as she hung up, Tony was racing to find out what to do. He laid out a blanket and pillows to sit on, but other than that, he had nothing. Maybe she wouldn't mind if he just laid out a bunch of snack food. Then he could just lay out some chips and dip. Or would she rather be healthier? He at least knew how to cut fruits and vegetables. Both?

He was tempted to call someone or go ask his dad, but decided against it. Because who knows what kind of crap he'll get for not even knowing how to set up a picnic. So, he sat at the table, contemplating what he could do.

He must have lost track of time, because suddenly there was a knock at the door. "Pepper!" Tony suddenly exclaimed in horror as he realized he wasn't ready yet. What was he going to tell her?

He rushed to the door, so he didn't make her wait, and opened the door. She was wearing her white coat that hugged her form perfectly in Tony's opinion with a really pretty red scarf, because after all, red was her favorite color. Her breath was silver in the cold air and her cheeks became a pretty shade of red. As always, she managed to steal his breath from right under his nose.

"Pepper," he breathed out lamely.

"Tony," she nodded. "Are you going to let me in?"

Tony shook his head and hurried to invite her inside. She walked into the heated home with a smile on her face. It was then that Tony realized that Pepper was holding something. It was always her hands that he noticed last. It was covered under a red blanket, and was big enough to be held with two hands.

He held out his hands to take the item from her hands for her. "What is that?" he asked as she handed it over to him. When it was completely in his hands, Tony realized it was warm.

"Food," Pepper smiled. "You and I both know that you can't cook."

Tony was too surprised to either take offense or pout in embarrassment. "How did you know?"

"I just had this feeling," Pepper told him. "Plus, I haven't eaten since lunch and you called before I could eat dinner."

Tony silently cheered. He hadn't called after she had eaten! To him, that was a big achievement. "Oh," was all that he could say though.

"So why did you call me here?" Pepper asked, her voice getting excited again.

Then Tony became speechless again. Now was the time for him to tell her. Tell her everything he had wanted to say. His feelings for her, how beautiful and smart she was, the whole deal. But his heart was in his throat again and he couldn't find the words. What he was about to say, really was going to change both of their lives for better or for worse. Even if he was exaggerating the results, he wasn't too keen of finding out that he was only going to be rejected.

Pepper was staring at him with her big brown eyes, the eyes that sparkled with curiosity and wonder. The same brown eyes he always found himself getting lost in. He had to say something, that he knew. But what? He'd been imagining this moment since this morning when he had decided that today was going to be the day. Today, this Valentine's Day, he was going to confess his feelings for his love. The one he had found himself falling in love for.

But was now really the time to be confessing? Was now really the time to be putting that sort of thing between them? He was starting to doubt that he even had it inside himself to do what he'd been hoping for all day. Actually for weeks now, since the first day he had realized that he had fallen in love with his best friend.

He thought about the chocolates he had waiting for Pepper upstairs in the living room. He thought about the movies he had bought for them to watch together while eating a indoor picnic. Were they going to go to waste because he couldn't brave telling Pepper the words he's been trying to tell her all day?

He thought about earlier that day on how he first chickened out. He'd made a fool of himself when he told Pepper that there was something on her face. There was, but that hadn't been what he wanted to tell her. He wanted to tell her how she made him feel and how her smile made him weak in the knees. Then he thought about the locker fiasco. He couldn't even manage to put the letter in the right locker.

But then, he thought of what his mom always said. It was something Tony never thought he'd be thinking about ever since she was gone. But for some reason, at this moment, he was remembering.

_"The third time's the charm," _She had always said after failing the first two times. Tony would laugh and tell her that he didn't believe in that sort of thing.

_The third time's the charm_, Tony thought to himself slowly. He repeated it in his mind a few times before a smile stretched across his lips. "The third time's the charm!" Tony verbalized unintentionally this time.

"What?" Pepper asked, not having expected that answer from him.

The first time he chicken out, the second time he royally screwed up, and the third time, well, hopefully his mother's favorite saying would be a grand success. His third try was going to be the charm. he just knew it.

"Pepper," Tony began boldly after taking in a big, deep breath. He was going to say it. He was going to tell her. "I have something I want to tell you and I'm not chickening out this time. Will you please hear me out?"

Pepper didn't really know what to say to Tony's sudden enthusiasm. His face was still red, but he looked ready. Ready for what, Pepper couldn't say yet. "Okay, I'll hear you out."

Tony's smile widened. "This may seem cheesy and lame, but it's Valentine's Day, so I'm excused. But you have a smile that challenges the sun. You have the most beautiful eyes in the whole world. You are incredibly smart and beyond amazing. I don't know how I hadn't seen any of this before. And I don't know how I haven't said anything before now. But here I am now, telling you that you have stolen my heart and I think, no, I _have _fallen for you." Tony took a quick breath before continuing. "And I have invited you here tonight to have some chocolates and to watch a romantic movie while eating an indoor picnic."

For a few moments, Tony feared that he might have gone a little far. But soon enough, Pepper's face lit up so much, Tony almost had to look away. She smiled, showing her teeth and all, and a long squeal of glee escaped her lips.

"Oh," Tony quickly added, "And will you be my girlfriend?"

Tony hadn't thought that Pepper's smile could get any more beautiful or blinding. But it did. And Tony hardly had time to set the picnic food out of the way before Pepper literally flung herself into his arms. Now, Tony's hugged Pepper before. They were friends after all. But before now, he hadn't realized how perfect she had fit in his arms. Almost like to puzzle pieces being placed together. She was just the perfect height to where he could just rest his chin over her head.

"Are you serious?" Pepper asked, not believing it herself. "Of course! Yes! I will!"

"So the third time really is the charm," Tony spoke to himself, when Pepper pulled away, her eyes shining a whole new way than moments before. _Thanks mom,_ he thought to himself looking up slightly.

"What?" Pepper asked.

Again Tony though about his last two failures earlier that day and laughed nervously. "Well..."

**Yay! Tony finally confessed! Ignore the cheesiness. It happens. :P **

**Fun Fact: _I_ _recently just dyed my hair orange-red. :)_**

**Hugs and Love, SilverPedals!**

**P.S. In regards to fun facts, I'm running out of things to tell you or ideas for fun facts that don't get repetitive. But I don't want to stop them. So, ask me a question that you want to know about me! I'll answer it in my upcoming fun facts! (As long as I'm comfortable with sharing what you're asking of me.)**


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